• Title/Summary/Keyword: Gallate

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The chemical structure of polyphenols isolated from cacao bean and their inhibitory effect on ACE (Cacao bean으로부터 분리된 polyphenol 성분의 화학구조분석과 ACE 저해효과)

  • Chang, Young-Youl;Yim, Moo-Hyun;Lee, Man-Chong
    • Applied Biological Chemistry
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    • v.41 no.1
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    • pp.110-117
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    • 1998
  • Seven kinds of polyphenol compounds having ACE activities were isolated and purified by Sephadex LH-20, MCI-gel CHP-20, ${\um}-Bondapak\;C_{18}$ and Fuji-gel ODS $G_3$ sucessively from cacao bean(Ghana). The chemical structures of each compound were determined and identified using analyzers such as $^1H-NMR$, $^{13}C-NMR$, IR, MS, polarimeter and Elemental Analysis. Inhibition effects of isolated polyphenols on angiotensin converting enzyme (concerned with hypertension) were also observed. The results obtained were as follows,; The compounds isolated and identified were confirmed and determined as compound 1 [(+)-catechin], compound 2 [(-)-epicatechin], compound 3 [procyanidin B-1 : (-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(+)catechin], compound 4 [procyanidin B-2 : (-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin], compound 5 [procyanidin B-7 : (-)-epicatechin-$(4{\beta}{\rightarrow}6)$-(+)-catechin], campound 6 (procyanidin B-2,3,3'-O -digallate), compound 7 [cinnamtannin A-2 : (-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin-$(4{\beta}{\rightarrow}8)$-(-)-epicatechin]. In the inhibition effect on ACE, procyanidin B-2,3,3'-O-digallate (compound 6) showed a higher value of 94.6% for ACE in $100\;{\um}M$ than other compounds such as (+)-catechin (compound 1), (-)-epicatechin (compound 2), procyanidin B-1 (compound 3), procyanidin B-2 (compound 4), procyanidin B-7 (compound 5) and cinnamtannin A-2 (compound 7) showing 67.9%, 61.9%, 88.6%, 82.5%, 72.2% and 82.3% for ACE, respectively. Inhibition of $4{\beta}{\rightarrow}8$ in coupling bond on the ACE enzyme was more effective than that of $4{\beta}{\rightarrow}6$. Procyanidin containing gallate inhibited more effectively than those containing not any. It was also observed that a lot of hydroxy group in the compounds increased the inhibitory effect.

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Antioxidative and biological activity of extracts from Orostachys japonicus (와송(Orostachys japonicus) 추출물의 항산화 및 생리 활성)

  • Lim, Sun-Mi;Park, Hye-Jin;Cho, Young-Je
    • Journal of Applied Biological Chemistry
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    • v.60 no.4
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    • pp.293-300
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    • 2017
  • This study was designed to extracts from Orostachys japonicas were investigated to assess anti-oxidation and biological activity. Phenolic content was maximum of $10.56{\pm}0.32mg/g$ when extracted with 50% ethanol. In anti-oxidative activity, Orostachys japonicus electric donating activity was higher than 80% in both water and ethanol extract at $200{\mu}g/mL$. 2,2'-Azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) radical cation decolorization of both water and ethanol extract was higher than 95.0% but antioxidant protection factor of water extract was higher than ethanol extract. Thiobarbituric acid reactive substance of ethanol extract was higher than water extract. For antihypertensive effect determination, angiotesin converting enzyme of water and ethanol extract showed 6.67 and 7.98% each at $200{\mu}g/mL$. Ethanol extract of $200{\mu}g/mL$ showed xanthin oxidase inhibitory effect of 60.85% but was not shown with water extract. Orostachys japonicus ethanol extract showed higher tyrosinase inhibitory activity of 64.59% which was higher than kojic acid of control indicating higher whitening effect. In anti-wrinkle effect, ethanol extract at $50-200{\mu}g/mL$ showed collagenase inhibitory effect of 75.95-85.02% which was higher than 68.91-76.64% of epigallocatechin-gallate of control group. 50% ethanol extract showed higher elastase inhibitory activity than water extract. Therefore, Orostachys japonicus extracts were identified to have high anti-wrinkle effect. These results identify anti-oxidative activity, gout prevention, whitening effect, and anti-wrinkle effect which indicate the possibility as a source for functional material.

A Comparative Study on Anthocyanin and Polyphenol Contents in Colored Agricultural Products (유색 농산물 중 안토시아닌과 폴리페놀 함량 비교 연구)

  • Jeong, Il-Hyung;Oh, Moon-Seog;Jeon, Jong-Sup;Kim, Han-Taek;Hong, Se-Ra;Park, Kwang-Hee;Yoon, Mi-Hye
    • Journal of Food Hygiene and Safety
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    • v.32 no.5
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    • pp.371-380
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    • 2017
  • In this study, 17 kinds of polyphenols and 5 kinds of anthocyanins were analyzed to compare the contents of polyphenols and anthocyanins in 76 colored agricultural products. A total of 17 polyphenols were analyzed simultaneously by 9 phenolic acids (gallic acid, protocatechuic acid, chlorogenic acid, vanillic acid, caffeic acid, syringic acid, p-coumaric acid, t-ferulic acid, t-cinnamic acid) and 8 flavonoids ((+)catechin, syringic aldehyde, rutin, epicatechin gallate, naringin, luteolin, naringenin, kaempferol) and 5 anthocyanins (delphinidin-3-glucoside, delphinidin-3-rutinoside, cyanidin-3-galactoside, cyanidin-3-glucoside, cyanidin-3-arabinoside) were simultaneously analyzed. The total content of 17 polyphenols was determined as seoritae $255.1{\pm}7.5{\mu}g/g$, seomoktae $275.8{\pm}5.3{\mu}g/g$, black rice $78.5{\pm}4.6{\mu}g/g$, black sesame $75.8{\pm}3.2{\mu}g/g$, blueberry $143.3{\pm}5.5{\mu}g/g$, aronia $195.2{\pm}4.9{\mu}g/g$ and blackcurrent $131.6{\pm}3.2{\mu}g/g$, the highest content was found in the order of seomoktae > seoritae > aronia > blueberry > blackcurrant > black rice > black sesame. The total content of 5 anthocyanins was determined as seoritae $82.4{\pm}17.2{\mu}g/g$, seomoktae $95.2{\pm}6.1{\mu}g/g$, black rice $74.1{\pm}9.7{\mu}g/g$, black sesame were not detected, blueberry $110.8{\pm}1.9{\mu}g/g$, aronia $218.9{\pm}6.1{\mu}g/g$ and blackcurrent $209.7{\pm}4.0{\mu}g/g$, the highest content was found in the order of aronia > blackcurrant > blueberry > seomoktae > seoritae > black rice. These results indicated that seomoktae and aronia possessed the high level of functional components and further study will be needed to develop high value-added foods based on the colored agricultural products.

Mechanisms for Anti-wrinkle Activities from Fractions of Black Chokeberries (블랙초크베리 분획물로부터의 주름억제 효과에 대한 작용기전)

  • Choi, Eun-Young;Kim, Eun-Hee;Lee, Jae-Bong;Do, Eun-Ju;Kim, Sang-Jin;Kim, Se-Hyeon;Park, Jeong-Yeol;Lee, Jin-Tae
    • Journal of Life Science
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    • v.26 no.1
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    • pp.34-41
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    • 2016
  • Black chokeberries (scientific name Aronia melanocarpa) have been reported to have major effects due to anti-oxidant, anti-inflammatory, and anti-cancer capabilities. In this study, we investigated the anti- wrinkle effects of A. melanocarpa, including collagenase inhibition effects and their molecular biological mechanisms, such as oxidative stress-induced matrix metalloproteinase (MMP), mitogen-activated protein (MAP) kinase, and activator protein (AP)-1 expression and/or phosphorylation. In collagenase inhibition activity, the ethyl acetate fraction of black chokeberry (AE) was 77.2% at a concentration of 500 μg/ml, which was a significant result compared to that of Epigallocatechin gallate (positive control, 83.9% in 500 μg/ml). In the reactive oxygen species (ROS) assay, the AE produced 78% of ROS in 10 μg/ml and 70% of ROS in 75 μg/ml, which was a much lower percentage than the ROS production of H2O2-induced CCRF S-180II cells. In the MTT assay, cell viability was increased dose-dependently with AE in H2O2-induced cells. In protein expression by western blot assay, the AE suppressed the expression and phosphorylation of MMPs (MMP-1, -3, -9), MAPK (ERK, JNK, and p38), and AP-1 (c-Fos and c-Jun), and expressed the pro-collagen type I in H2O2-induced cells. These results suggest that black chokeberries have anti-wrinkle and collagen-production effects, and they may be used in applications for material development in the functional food and cosmetic industries.

Combining Ginsenoside F1 with (-)-Epigallocatechin Gallate Synergistically Protects Human HaCaT Keratinocytes from Ultraviolet B-Induced Apoptosis (Ginsenosdie F1과 EGCG의 상승작용에 의한 자외선조사에 의한 세포 사멸 방지)

  • Tae Ryong, Lee;Si Young, Cho;Eun Hee, Lee;Myeong Hoon, Yeom;Ih-Seop, Chang
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.30 no.2
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    • pp.253-261
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    • 2004
  • Ginsenosides and green tea extracts show a variety of biomedical efficacies such as anti-aging, anti-oxidation and anti-tumor-promotion effects. (-)-Epigallocatechin-3-gallate (EGCG) has been reported to inhibit the UVB-induced apoptosis by increasing the Bcl-2-to-Bax ratio. We have previously shown that ginsenoside Fl protects human HaCaT cells from ultraviolet-B (UVB)-induced apoptosis by maintaining constant levels of Bcl-2 and Brn-3a. Here, we investigate the combined effect of ginsenoside Fl and EGCG on the protection of human HaCaT keratinocyte against UVB-induced apoptosis. When treated individually, although 5 ${\mu}$M ginsenoside Fl and 50${\mu}$M EGCG protected cells from UVB-induced apoptosis, 2${\mu}$M ginsenoside Fl or 10${\mu}$M EGCG treatment showed very little protection effect. However, cotreatement of 2${\mu}$M ginsenoside Fl and 10${\mu}$M EGCG successfully protected HaCaT cells from UVB-induced cell death. As expected, combining ginsenoside Fl and EGCG efficiently prevented UVB-induced decrease of Bcl-2 and Brn-3a expression. In addition, cotreatment with ginsenoside F1 and EGCG prevented the dephosphorylation of Rb, whereas individual treatment with ginsenoside Fl or EGCG failed to prevent the dephosphorylation of Rb even at high concentrations.

Change of physicochemical properties, phytochemical contents and biological activities during the vinegar fermentation of Elaeagnus multiflora fruit (보리수 열매 식초 발효 중 이화학적 특성, phytochemical 함량 및 생리활성 변화)

  • Cho, Kye Man;Hwang, Chung Eun;Joo, Ok Soo
    • Food Science and Preservation
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    • v.24 no.1
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    • pp.125-133
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    • 2017
  • This study evaluated the changes of physiochemical properties, phytochemical contents, and biological activities during the vinegar fermentation of Elaeagnus multiflora fruit. The contents of pH and reducing sugar decreased from 3.55 and 6.88 mg/mL 3.34 and 2.13 mg/mL, respectively. However the acidity increased from 0.48% to 5.48% during the vinegar fermentation. The alcohol contents increased up to a maximum value of 6.6% at 20 days, and it then decreased at the end fermentation days (2.0%). The viable numbers of acetic acid bacteria and yeasts increased from 4.32 log CFU/mL and 3.23 log CFU/mL at 10 days to 5.4 log CFU/mL and 5.5 log CFU/mL during the spontaneous fermentation, respectively. The major organic acids were acetic acid (38.84 mg/mL), lactic acid (4.92 mg/mL), and malic acid (1.51 mg/mL). The soluble phenolic and flavonoid contents increased from 0.79 mg/mL and 0.12 mg/mL of initial fermentation day to 1.22 mg/mL and 0.14 mg/mL during the spontaneous fermentation. Content of epicatechin gallate decreased from $168.1{\mu}g/mL$ at 10 days to $115.97{\mu}g/mL$. However the content of gallic acid increased from $18.52{\mu}g/mL$ to $95.07{\mu}g/mL$ during fermentation. After 60 days of the fermentation, the antioxidant and digestive enzyme inhibitory activities were 71.35% (DPPH), 79.27% (ABTS), 68.72% (${\cdot}OH$), 85.42% (${\alpha}$-glucosidase), 52.12% (${\alpha}$-amylase), and 53.66% (pancreatic lipase), respectively.

Comparative Analysis of Catechins and Antioxidant Capacity in Various Grades of Organic Green Teas Grown in Boseong, Korea (보성산 유기농 녹차의 품질에 따른 카테킨 함량과 항산화능 비교 분석)

  • Park, Kyung-Ryun;Lee, Sang-Gil;Nam, Tae-Gyu;Kim, Young-Jun;Kim, Young-Rok;Kim, Dae-Ok
    • Korean Journal of Food Science and Technology
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    • v.41 no.1
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    • pp.82-86
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    • 2009
  • The objective of this study was to evaluate the effect of various solvents on extraction of bioactive phenolics and to analyze the antioxidant capacity and contents of individual catechins in various grades of green teas organically grown in Boseong, Korea. The organic green teas, based on their harvest seasons, were categorized into five grades such as Woo-Jeon, Se-Jak, Jung-Jak, Dae-Jak, and coarse tea. Solvents used to extract phenolics from these teas included water at $23^{\circ}C$ and $70^{\circ}C$ as well as 80% (v/v) aqueous methanol and ethanol. In general, aqueous organic solvents of methanol and ethanol led to higher extraction yields of phenolics than water at $23^{\circ}C$ and $70^{\circ}C$. Total phenolics and antioxidant capacity of the teas extracted with the aqueous organic solvents were approximately 1.5 to 3.2 and 1.8 to 3.8 times higher than those with water at $23^{\circ}C$ and $70^{\circ}C$, respectively. Coarse tea, the lowest grade of green tea, showed approximately 30-60% lower total phenolics and antioxidant capacity compared with the higher grade ones. Reversed-phase HPLC analysis was performed quantitatively to identify individual catechins, gallic acid, and caffeine in teas extracted with 80% (v/v) aqueous methanol. Based on their dry weights, the organic green teas contained about 1.7 to 2.9% of caffeine. Content (mg/g dry weight) of tea catechins decreased in the following order: Woo-Jeon (155.4) > Se-Jak (147.7) > Jung-Jak (143.2) > coarse tea (135.1) > Dae-Jak (130.5). (-)-Epigallocatechin gallate was the most abundant among the catechins analyzed. The highest grade of green tea, Woo-Jeon, had the highest amount of (-)-epigallocatechin gallate at 77.4 mg/g dry weight. Overall, the higher grade of organic green teas tended to have the higher level of antioxidant capacity and catechins.

Antioxidant and Antiwrinkle Effects of Persimmon Leaves extract (시엽(Persimmon Leaves) 에탄올 추출물의 항산화와 항주름 효과)

  • Sung-Hee Kim;Dong-Hee Kim;Wi-Hye Yeon;Jin-Tae Lee;Young-Ah Jang
    • Journal of the Korean Applied Science and Technology
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    • v.40 no.3
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    • pp.534-546
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    • 2023
  • In this study, we investigated the antioxidant and anti-winkle activity in human fibroblast cell (CCD-986sk) of Persimmon Leaves (PL) as a cosmetic ingredient. As a result of investigating antioxidant activity through electron-donating ability and ABTS+ radical scavenging assay, the PL showed concentration-dependent antioxidant activity similar to ascorbic acid, a control group, at a concentration of 1,000 ㎍/ml. As a result of investigating the anti-wrinkle effect through elastase inhibition and collagenase inhibition assay, the PL showed concentration-dependent antioxidant activity similar to epigallocatechin gallate, a control group, at a concentration of 1,000 ㎍/ml. As a result of measuring the synthesis rate of pro-collagen type I and the inhibition rate of MMP-1 in UVB-induced CCD-986sk cells, the control group EGCG showed a 90.2% pro-collagen synthesis rate at 20 ㎍/ml and PL showed an 88.5% synthesis rate at 30 ㎍/ml. In addition, the inhibition rate of MMP-1 of 33.0% and 40.8% were confirmed in EGCG 20 ㎍/ml and PL 30 ㎍/ml, respectively. As a result of measuring the protein expression of pro-collagen type I and MMP-1 in the PL through western blot, it was confirmed that the protein expression of pro-collagen type I increased, and MMP-1 decreased when the PL was treated together compared to the UVB alone group. According to the above experimental results, it is expected to be used as a natural product material for cosmetics by confirming that the PL prevent photoaging caused by UVB stimulation and have antioxidant and anti-wrinkle effects.

Factors Affecting Reactivity of Various Phenolic Compounds with the Folin-Ciocalteu Reagent (다양한 페놀성 물질과 Folin-Ciocalteu 시약의 반응성에 미치는 영향 요인 평가)

  • Hong, Jung-Il;Kim, Hyun-Jung;Kim, Ji-Yun
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.40 no.2
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    • pp.205-213
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    • 2011
  • The Folin-Ciocalteu (F-C) reagent has been extensively used for quantifying total phenolic contents in many different types of food materials. Since several different procedures of the assay methods using the F-C reagent have been applied, we investigated changes in reactivity of various phenolic compounds with the F-C reagent under three different assay conditions and factors affecting reactivity. Among 10 standard compounds tested, compounds with high hydroxyl density (number of -OH/molecular weight) showed a largely different response according to addition sequence of the F-C reagent or $Na_2CO_3$. Preincubation in $Na_2CO_3$ significantly reduced the reactivity of the phenolic compounds bearing galloyl moiety (e.g. gallic acid, tannic acid, and epigallocatechin-3-gallate) with the F-C reagent, while monophenol compounds including ferulic acid and sinapinic acid were more stable as compared to diphenols. There was little change in response to the F-C reagent of all phenolic compounds incubated in acidic pH; their reactivity except ferulic acid was reduced significantly when incubated in neutral or alkaline pH. Changes in reactivity of gallic acid incubated in $Na_2CO_3$ or neutral/alkaline pH conditions were the most prominent. $H_2O_2$ generated from phenolic compounds did not affect the reaction with the F-C reagents. The present results suggest that reactivity of different phenolic compounds with F-C reagent was affected considerably by different procedures of the assay, and the total phenolic contents could be fluctuated according to standard compounds and assay scheme.

Antioxidant Activity of Chestnut (Castanea crenata S.et Z.) bur Fermented by Lactobacillus casei (유산균 발효에 의한 밤송이추출물의 항산화 효과)

  • Jun, Dong Ha;Cho, Woo-A;Lee, Jae Bong;Jang, Min Jung;You, Mi Suk;Park, Jung Youl;Kim, Sea Hyun;Lee, Jin Tae
    • Journal of Life Science
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    • v.24 no.11
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    • pp.1193-1199
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    • 2014
  • The aim of this study was to show the antioxidant properties of chestnut (Castanea crenata) bur extracts fermented by Lactobacillus casei. The chestnut has been used as a cosmetic material in Korea for many years. This study showed that reactive oxygen species (ROS) were inhibited by the fermentation materials of chestnut bur extracts. The antioxidant activities were analyzed and expressed as EDA, ABTS, reducing power, SOD-like activity, hydrogen peroxide scavenging activity, superoxide anion radical scavenging activity, and nitric oxide scavenging ability. The antioxidant activities of fermentation materials from L. casei of chestnut bur extracts were higher than those of butylated hydroxyanisole (BHA), epigallocatechin gallate (EGCG), and ascorbic acid (AA). Therefore, we expect that fermentation materials from L. casei of chestnut bur extracts are valuable resources as natural antioxidants and functional cosmetics ingredients.